In an outbound contact center, a contact center agent/customer interaction may result in the customer requesting a callback at a preferred window (e.g., a video conference callback next Thursday @ 1:00 P.M). In such cases, the requested callback window is stored by an autodialer that automatically dials the customer within the callback window so that the customer and the same contact center can continue their conversation. Since the customer has provided the preferred time, it becomes important to connect to the customer during the preferred callback window. However, the preferred callback window may coincide with other events of the contact center agent. For example, the contact center agent may have an upcoming meeting during the preferred callback window. This may result in the callback not being made within the preferred callback window.